Water → HCID 67790986, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl)-3-methyl-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (0.33 g) and triethylamine (0.17 ml ) in dichloromethane (10 ml) was added allyl oxalyl chloride (0.13 g) at -20° C. and the resulting mixture was stirred for 30 minutes at -20° C. The reaction mixture was taken up into a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, washed in turn with water, aqueous sodium hydrogen carbonate and brine, and dried over magnesium sulfate. Evaporation of the solvent gave allyl 2-[(3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]- 3-{(1R)-1-t-butyldimethylsilyloxyethyl)-2-oxoazetidin-1-yl]glyoxylate (0.26 g).

Provenance & Evidence